TBAF tetrahydrofuran → 4-(2-Hydroxyethyl)pyridine-2-carbonitrile

4-[2-(tert-Butyldimethylsiloxy)ethyl]pyridine-2-carbonitrile (6.5 g, 24.8 mmol) obtained in Step 3 was dissolved in THF (100 mL), then a TBAF-THF solution (1.00 mol/L, 49.6 mL, 49.6 mmol) was added thereto, followed by stirring at room temperature for 10 hours. After completion of the reaction was confirmed by thin-layer chromatography, the reaction mixture was concentrated under reduced pressure. The concentrate was diluted with ethyl acetate, water was added thereto, and the mixture was separated into organic layer and aqueous layer. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give 4-(2-hydroxyethyl)pyridine-2-carbonitrile (2.53 g, yield 69%).

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. additionThe concentrate was diluted with ethyl acetate, water
3. additionwas added
4. customthe mixture was separated into organic layer and aqueous layer
5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (ethyl acetate)

ORD record

ord-2f2739da71784ec1b8842ef31208a155

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07956060B2